Methanol → HCID 69331780, compound

HRID 1374983Notes

Reaction equation

HRID 1374983 reaction equation
S(Cl)([Cl:3])=O.Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=1[CH3:20])[CH2:11][C@H:12]([C:14]([OH:16])=[O:15])[NH2:13].[CH3:21]O>>[ClH:3].[CH3:21][O:15][C:14](=[O:16])[C@@H:12]([CH2:11][C:10]1[CH:17]=[CH:18][C:19]([CH3:20])=[C:8]([O:7][CH3:6])[CH:9]=1)[NH2:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 69331765HCID 69331765, compound

Product 1

HCID 69331780HCID 69331780, compound

Procedure

Thionyl chloride (0.7 ml) was added dropwise to a solution of 3-methoxy-4-methyl-D-phenylalanine hydrochloride (1.75 g) in methanol (8 ml) over 10 minutes at room temperature. The whole was stirred at 40–50° C. for 2 hours and then an additional thionyl chloride (0.7 ml) was added to the mixture. The whole mixture was stirred for further 1 hour and evaporated under reduced pressure. The resulting solid was triturated with diisopropyl ether and collected by filtration to give colorless crystals of 3-methoxy-4-methyl-D-phenylalanine methyl ester hydrochloride (1.70 g).

Workup

  1. stirringThe whole mixture was stirred for further 1 hour
  2. customevaporated under reduced pressure
  3. customThe resulting solid was triturated with diisopropyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a6a37df20b3b4a339af7001d15b6716d
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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